408352-58-9

Basic information

• Product Name: 2,6-Dibromo-4-cyanopyridine
• Synonyms: 2,6-Dibromo-4-cyanopyridine
• CAS NO: 408352-58-9
• Molecular Formula: C6H2 Br2 N2
• Molecular Weight: 261.9
• Mol File: 408352-58-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 280.8±35.0 °C(Predicted)
• Appearance: /
• Density: 2.19±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -7.02±0.10(Predicted)
• CAS DataBase Reference: 2,6-Dibromo-4-cyanopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dibromo-4-cyanopyridine(408352-58-9)
• EPA Substance Registry System: 2,6-Dibromo-4-cyanopyridine(408352-58-9)

Safety Data

• Hazardous Substances Data: 408352-58-9(Hazardous Substances Data)

Usage

General Description

2,6-Dibromo-4-cyanopyridine is a chemical compound with the molecular formula C6H2Br2N2. It is a yellowish-brown crystalline powder that is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. 2,6-Dibromo-4-cyanopyridine is reactive and can undergo various chemical reactions, including nucleophilic substitution and aromatic substitution. It is also known for its high level of toxicity and should be handled with care. In addition, 2,6-Dibromo-4-cyanopyridine is flammable and should be stored and handled in a well-ventilated area away from heat and open flames.

Upstream product

• 32710-65-9 2,6-dichloro-4-cyanopyridine 

Downstream Products

• 223463-02-3 2,6-dibromo-4-(hydroxymethyl)pyridine 
• 408352-56-7 C-(2,6-dibromo-[4]pyridyl)-methylamine 

Relevant articles and documents

Synthesis and evaluation of heterocyclic analogues of bromoxynil

One attractive strategy to discover more active and/or crop-selective herbicides is to make structural changes to currently registered compounds. This strategy is especially appealing for those compounds with limited herbicide resistance and whose chemistry is accompanied with transgenic tools to enable herbicide tolerance in crop plants. Bromoxynil is a photosystem II (PSII) inhibitor registered for control of broadleaf weeds in several agronomic and specialty crops. Recently at the University of Tennessee - Knoxville several analogues of bromoxynil were synthesized including a previously synthesized pyridine (2,6-dibromo-5-hydroxypyridine-2-carbonitrile sodium salt), a novel pyrimidine (4,6-dibromo-5-hydroxypyrimidine-2-carbonitrile sodium salt), and a novel pyridine N-oxide (2,6-dibromo-1-oxidopyridin-1-ium-4-carbonitrile). These new analogues of bromoxynil were also evaluated for their herbicidal activity on soybean (Glycine max), cotton (Gossypium hirsutum), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), large crabgrass (Digitaria sanguinalis), and pitted morningglory (Ipomoea lacunose) when applied at 0.28 kg ha-1. A second study was conducted on a glyphosate-resistant weed (Amaranthus palmeri) with the compounds being applied at 0.56 kg ha -1. Although all compounds were believed to inhibit PSII by binding in the quinone binding pocket of D1, the pyridine and pyridine-N-oxide analogues were clearly more potent than bromoxynil on Amaranthus retroflexus. However, application of the pyrimidine herbicide resulted in the least injury to all species tested. These variations in efficacy were investigated using molecular docking simulations, which indicate that the pyridine analogue may form a stronger hydrogen bond in the pocket of the D1 protein than the original bromoxynil. A pyridine analogue was able to control the glyphosate-resistant Amaranthus palmeri with >80% efficacy. The pyridine analogues of bromoxynil showed potential to have a different weed control spectrum compared to bromoxynil. A pyridine analogue of bromoxynil synthesized in this research controlled several weed species greater than bromoxynil itself, potentially due to enhanced binding within the PSII binding pocket. Future research should compare this analogue to bromoxynil using optimized formulations at higher application rates.